D-erythro-Sphingosine

Names

[ CAS No. ]:
123-78-4

[ Name ]:
D-erythro-Sphingosine

[Synonym ]:
EINECS 204-651-3
(4E)-sphing-4-enine
D-erythro-Sphingosine,synthetical
BRAIN,BOVINE
MFCD00036751
Sphingosine, D-erythro
DErySphingosine
[3H]-Sphingosine
4-trans-Sphingenine
Sphingosine
4-Sphingenine
[Fluorescein]-Sphingosine
(2S,3R,4E)-2-Aminooctadec-4-ene-1,3-diol
Sphingenine
EGG SPHINGOSINE
D-erythro-Sphingosine
D-Sphingosine
4-Octadecene-1,3-diol, 2-amino-, (2S,3R,4E)-
erythro-4-Sphingenine
CEREBROSIDE
(2S,3R,4E)-2-Amino-4-octadecene-1,3-diol
(-)-D-erythro-Sphingosine
(2S,3R,4E)-2-amino-3-hydroxyoctadec-4-ene-1-ol
BRAIN SPHINGOSINE
(4E)-sphingenine
trans-4-sphingenine
D-erythrosphingosine
C18-Sphingosine
(2S,3R,E)-2-Amino-4-octadecene-1,3-diol
Sphingosine 2S,3R,2S,3R,4E)-2-aminooctadec-4-ene-1,3-diol
UNII:0Y6SVQ612Q
(4E)-2-Aminooctadec-4-ene-1,3-diol

Biological Activity

[Description]:

D-erythro-Sphingosine is a very potent activator of p32-kinase with an EC50 of 8 μM. D-erythro-Sphingosine inhibits protein kinase C (PKC).

[Related Catalog]:

Research Areas >> Cancer

Natural Products >> Others

[Target]

p32:8 μM (EC50)

PKC

Human Endogenous Metabolite

[In Vitro]

A p32-sphingosine-activated protein kinase responds to low concentrations of D-erythro-Sphingosine with an initial activation observed at 2.5 μM and a peak activity at 10-20 μM. This kinase shows a modest specificity for D-erythro-Sphingosine over other sphingosine tereoisomers, and a preference for sphingosines over ihydrosphingosines[1]. D-erythro-Sphingosine inhibits protein kinase C in vitro[2]. D-erythro-Sphingosine has been shown to inhibit protein kinase C, which affects cell regulation and several signal transduction pathways, and exhibits antitumor promoter activities in various mammalian cells[3].

[References]

[1]. Pushkareva MYu, et al. Regulation of sphingosine-activated protein kinases: selectivity of activation by sphingoid basesand inhibition by non-esterified fatty acids. Biochem J. 1993 Sep 15;294 ( Pt 3):699-703.

[2]. Khan WA, et al. Protein kinase C and platelet inhibition by D-erythro-Sphingosine: comparison with N,N-dimethylsphingosine and commercial preparation. Biochem Biophys Res Commun. 1990 Oct 30;172(2):683-91.

[3]. Pham VT, et al. A concise synthesis of a promising protein kinase C inhibitor: D-erythro-Sphingosine. Arch Pharm Res. 2007 Jan;30(1):22-7.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
0.9±0.1 g/cm3

[ Boiling Point ]:
445.9±45.0 °C at 760 mmHg

[ Melting Point ]:
81-82ºC

[ Molecular Formula ]:
C₁₈H₃₇NO₂

[ Molecular Weight ]:
299.492

[ Flash Point ]:
223.5±28.7 °C

[ Exact Mass ]:
299.282440

[ PSA ]:
66.48000

[ LogP ]:
6.40

[ Vapour Pressure ]:
0.0±2.4 mmHg at 25°C

[ Index of Refraction ]:
1.489

[ Water Solubility ]:
chloroform: 20 mg/mL

MSDS

Click to get detail MSDS

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Safety Phrases ]:
22-24/25

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ HS Code ]:
2922199090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2922199090

[ Summary ]:
2922199090. other amino-alcohols, other than those containing more than one kind of oxygen function, their ethers and esters; salts thereof. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%

Articles

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Breast Cancer Res. Treat. 149(1) , 59-67, (2015)

Obesity is a known risk factor for breast cancer. We have recently identified that adipokine leptin regulates the expression of a proto-oncogenic enzyme sphingosine kinase 1 (SK1). Signal transducer a...

Sphingosine kinase 1 isoform-specific interactions in breast cancer.

Mol. Endocrinol. 28(11) , 1899-915, (2014)

Sphingosine kinase 1 (SK1) is a signaling enzyme that catalyzes the formation of sphingosine-1-phosphate. Overexpression of SK1 is causally associated with breast cancer progression and resistance to ...

Fungal metabolite myriocin promotes human herpes simplex virus-2 infection.

Life Sci. 120 , 31-8, (2015)

Myriocin is a fungal metabolite with antiviral activity, including influenza, hepatitis B, and hepatitis C viruses. We investigated whether myriocin has activity against human HSV-2, one of the most p...